Photochromic naphthacenequinones, process for their preparation and the use thereof

Abstract

Compounds of formula I or V or mixtures thereof ##STR1## wherein R is unsubstituted C 6 -C 14 aryl or C 6 -C 14 aryl which is substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, phenyl, benzyl, --CN, --CF 3 , halogen or --COOR 5 , and R 5 is H, C 1 -C 18 alkyl, cyclohexyl, cyclopentyl, phenyl, C 1 -C 12 alkylphenyl, benzyl or C 1 -C 12 alkylbenzyl, and at least one of the substituents R 1 to R 4 is --F, --Cl or --Br, or is independently the group RO--, and the other substituents R 1 to R 4 are H, --F, --Cl or --Br, are reversible photochromic systems which can be used for contrast formation, light absorption or for the reversible optical storage of information.

What is claimed is: 
     
       1. A composition which comprises (a) a substrate which is a colorless organic solvent, a polymer, an organic glass or a compound glass; and   (b) a compound of the formula I or a mixture thereof ##STR10## wherein R is unsubstituted C 6  -C 14  aryl or C 6  -C 14  aryl which is substituted by C 1  -C 12  alkyl, C 1  -C 12  alkoxy, C 1  -C 12  alkylthio, phenyl, benzyl, --CN, --CF 3 , halogen or --COOR 5 , and R 5  is H, C 1  -C 18  alkyl, cyclohexyl, cyclopentyl, phenyl, C 1-C   12  alkylphenyl, benzyl or C 1  -C 12  alkylbenzyl, and at least one of the substituents R 1  to R 4  is --F, --Cl or --Br, or is independently the group RO--, and the other substituents R 1  to R 4  are H, --F, --Cl or --Br; which compound of formula I is dissolved in the substrate, incorporated in the substrate, or present on at least one surface of the substrate.   
     
     
       2. A composition according to claim 1, wherein R in formula I is unsubstituted or substituted C 6  -C 10  aryl. 
     
     
       3. A composition according to claim 2, wherein R is unsubstituted or substituted phenyl or 1- or 2-naphthyl. 
     
     
       4. A composition according to claim 1, wherein R in formula I is unsubstituted or substituted by C 1  -C 4  alkyl, C 1  C 4  alkoxy, C 1  -C 4  alkylthio, --F, --Cl, --Br or --COOR 5 , wherein R 5  is H or C 1  -C 18  alkyl. 
     
     
       5. A composition according to claim 1, wherein at least one of the substituents R 1  to R 4  in formula I is a group RO-- or --F, --Cl or --Br, and the other substituents R 1  to R 4  are H. 
     
     
       6. A composition according to claim 1, wherein R 1  or R 4 , or R 1  and R 3  or R 4 , or R 1  and R 2  or R 2  to R 4  is a group RO--, --F, --Cl or --Br. 
     
     
       7. A composition according to claim 1, wherein R 1  or R 4 , or R 1  and R 3  or R 4 , or R 1  and R 2  or R 1  to R 4  is a group RO-- or --Cl. 
     
     
       8. A composition according to claim 1, wherein R is unsubstituted phenyl. 
     
     
       9. A composition according to claim 1, wherein the compound of formula I is selected from the group consisting of 6,11-diphenoxy-2-chloronaphthacene-5,12-dione, 2,6,11-triphenoxynaphthacene-5,12-dione, 6,11-diphenoxy-2,3,8,9-tetrachloroaphthacene-5,12-dione and 2,3,6,8,9,11-hexaphenoxynaphthacene-5,12-dione. 
     
     
       10. A composition which comprises (a) a colorless substrate which is an organic solvent, a polymer, an organic glass or a compound glass; and   (b) a compound of the formula V or a mixture thereof ##STR11## wherein R is unsubstituted C 6  -C 14  aryl or C 6  C 14  aryl which is substituted by C 1  -C 12  alkyl, C 1  -C 12  alkoxy, C 1  -C 12  alkylthio, phenyl, benzyl, --CN, --CF 3 , halogen or --COOR 5 , and R 5  is H, C 1  -C 18  alkyl, cyclohexyl, cyclopentyl, phenyl, C 1  -C 12  alkylphenyl, benzyl or C 1  -C 12  alkylbenzyl, and at least one of the substituents R 1  to R 4  is --F, --Cl or --Br, or is independently the group RO--, and the other substituents R 1  to R 4  are H, --F, --Cl or --Br; which compound of formula V is dissolved in the substrate, incorporated in the substrate, or present on at least one surface of the substrate.